Hydrochloric Acid → 2-(4-Chlorophenyl)benzoxazole-4-carboxylic acid

HRID 506236노트

반응식

HRID 506236 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([O:19]C)=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:4][CH:3]=1.C1COCC1.[OH-].[Li+].Cl>C(OCC)(=O)C.O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:9][C:10]3[C:11](=[C:13]([C:17]([OH:19])=[O:18])[CH:14]=[CH:15][CH:16]=3)[N:12]=2)=[CH:6][CH:7]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68459315Methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate

생성물 1

HCID 596258542-(4-Chlorophenyl)benzoxazole-4-carboxylic acid수율 90.3%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A 100 mL round bottom flask equipped with a magnetic stirrer was charged with methyl 2-(4-chlorophenyl)benzoxazole-4-carboxylate (0.50 g, 1.74 mmol), THF (10 mL), methanol (10 mL), lithium hydroxide (0.08 g, 3.48 mmol) and water (10 mL). The reaction was stirred at room temperature for 18 hours. After this time, the reaction was diluted with ethyl acetate (50 mL) then acidified to pH 4 with 2 N HCl. The aqueous layer was extracted with ethyl acetate (2×25 mL). The organic layers were then combined and washed with brine (1×25 mL), dried with sodium sulfate, filtered and concentrated to dryness in vacuo to yield 2-(4-chlorophenyl)benzoxazole-4-carboxylic acid (0.43 g, 90% yield) as a white solid: 1H NMR (500 MHz, CDCl3) δ 11.53 (bs, 1H), 8.26 (d, J=8.5 Hz, 2H), 8.18 (d, J=8.0 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.55 (t, J=8.0 Hz, 1H); MS (ESI) m/z 274 [M+H]+

후처리

  1. customA 100 mL round bottom flask equipped with a magnetic stirrer
  2. extractionThe aqueous layer was extracted with ethyl acetate (2×25 mL)
  3. washwashed with brine (1×25 mL)
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-abde0d572f164f278a125d46e7c1dae4
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781430B2

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